Isolation and characterization of miscellaneous secondary metabolites of Deprea subtriflora

Two new C-18 norwithanolides based on a C(27) skeleton, subtrifloralactones K (1) and L (2), a new C-18 oxygenated withanolide, 13 beta-hydroxymethylsubtrifloralactone E (3), and a new alpha-ionone derivative, (+)-7 alpha,8 alpha-epoxyblumenol B (4), along with five known compounds, philadelphicalac...

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Bibliographic Details
Published in:Journal of natural products (Washington, D.C.) D.C.), 2003-08, Vol.66 (8), p.1089-1093
Main Authors: Su, B.N, Park, E.J, Nikolic, D, Vigo, J.S, Graham, J.G, Cabieses, F, Van Breemen, R.B, Fong, H.H.S, Farnsworth, N.R, Pezzuto, J.M
Format: Article
Language:English
Subjects:
13beta-hydroxymethylsubtrifloralactone
7alpha,8alpha-epoxyblumenol
Animals
Biological and medical sciences
carbon
Carcinoma, Hepatocellular
chemical structure
Deprea subtriflora
Drug Screening Assays, Antitumor
ergosterol
General pharmacology
Heterocyclic Compounds, 4 or More Rings - chemistry
Heterocyclic Compounds, 4 or More Rings - isolation & purification
Heterocyclic Compounds, 4 or More Rings - pharmacology
isolation
ketones
lactones
Lactones - chemistry
Lactones - isolation & purification
Lactones - pharmacology
Medical sciences
methylene
Mice
Molecular Structure
NAD(P)H Dehydrogenase (Quinone)
NADH or NADPH oxidoreductases
norwithanolides
Nuclear Magnetic Resonance, Biomolecular
Pharmacognosy. Homeopathy. Health food
Pharmacology. Drug treatments
phytochemicals
plant extracts
protons
quinone reductase
secondary metabolites
Solanaceae
Solanaceae - chemistry
Solanaceae - metabolism
spectral analysis
stereochemistry
Stereoisomerism
subtrifloralactones
Tumor Cells, Cultured
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Summary:Two new C-18 norwithanolides based on a C(27) skeleton, subtrifloralactones K (1) and L (2), a new C-18 oxygenated withanolide, 13 beta-hydroxymethylsubtrifloralactone E (3), and a new alpha-ionone derivative, (+)-7 alpha,8 alpha-epoxyblumenol B (4), along with five known compounds, philadelphicalactone A (5), (2S,3S,4R)-2-[(2R)-2'-hydroxytetracosanoylamino]-1,3,4-octadecanetriol (6), trans-N-feruloyltyramine, cis-N-feruloyltyramine, and (S)-coriolic acid, were isolated from additional active fractions of the chloroform-soluble extract of Deprea subtriflora, using a quinone reductase (QR) induction assay as a monitor. The structures of compounds 1-4 were characterized by spectroscopic data interpretation. The potential cancer chemopreventive activities of all isolates in terms of their ability to induce QR activity with cultured Hepa 1c1c7 mouse hepatoma cells were evaluated.
ISSN:0163-3864
1520-6025
DOI:10.1021/np030081n